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Caribbean vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Caribbean

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost
Home in San Cayetano de Venecia, Costa Rica
Quinta La Ceiba Modern Home with Pool in DairyFarm
A contemporary roomy vacation home situated in a dairy farm. Embrace serenity, unwind in a tranquil haven surrounded by cows grazing in lush green fields. It's a birdwatcher's paradise too. This is an ideal escape to disconnect and reconnect with nature. Dine and lounge outdoors make the most of the property's features. Our in-house travel concierge will be glad to arrange tours and activities for you at no additional cost. Consider our private chef service for an even more memorable experience.
$200 per night
Superhost
Condo in Miami, Florida
ICON 2B/2B Skyline Free Pool, Spa, HotTub
INSTA READY, This unit provides over 1,350SqFt of breathtaking ocean and city views with Two Bedrooms and Two Bathrooms. Located within the luxurious Icon building. The Icon is a 5 star condominium. It is located inside the heart of Downtown Miami/ Brickell. It includes the same amenities as the W Hotel, such as free access to spa, pool, hot tub, and 4 restaurants, including Cipriani. The apartment comes with three flat screen TVs, HighSpeed WiFi, and toiletries. As well as four separate beds.
$344 per night
Superhost
Bus in Tierras Morenas, Costa Rica
Sunset view BUS #1 near lake Arenal
Ideal for travelers that are looking for something unique! We converted an old bus to a great experience bringing mini apartment with a view. Bus is located next to our wood shop but we installed a good insulation to make sure you would't hear us working. You will have a complete privacy since all the windows are facing a nice valley of fields and sometimes cows. We made sure you could work remotely too, WIFI is fast. Follow us on IG: santos_skoolie
$128 per night

Private vacation rentals in Caribbean

Superhost
Houseboat in Key West, Florida
The Tiki Suite - soon to be a Key West icon
$485 per night
Superhost
Dome in Alajuela, Costa Rica
NEW Sukha Dome, near Poas Volcano & SJO Airprt
$90 per night
Superhost
Hut in Bavaro, Dominican Republic
Hut #1 Romantic Luxury Beachfront
$149 per night
Superhost
Tiny home in Sarasota, Florida
@Shellmateisland |tiny home| island| bikes| kayaks
$135 per night
Superhost
Condo in Montego Bay, Jamaica
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
$189 per night
Superhost
Villa in Montego Bay, Jamaica
VIBES COVE enjoy your stay while getting pampered
$704 per night
Superhost
Villa in Monteverde, Costa Rica
Monteverde Million Dollar View Eco-Villa
$395 per night
Superhost
Loft in Poás, Costa Rica
Loft & Jacuzzi - Póas - con vista VillaGuadalupe
$93 per night
Superhost
Home in DO, Dominican Republic
Beautifull Guest House with panoramic views
$261 per night
Superhost
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
$395 per night
Superhost
Guesthouse in Key Largo, Florida
Bayside Cabin beach romantic sunsets & fishing.
$194 per night
Superhost
Home in La Habana, Cuba
Casa Colonial 1922-Entire apartment-DATA internet
$195 per night

House rentals in Caribbean

Superhost
Home in Borinquen, Puerto Rico
The Nest at Crash Boat. Only waterfront on Beach
$321 per night
Superhost
Home in Nassau, Bahamas
Sunrise by the Sea - the ocean on your doorstep!
$445 per night
Superhost
Home in Hollywood, Florida
Pool House 3B/2B King Bed EV-Charger Hollywood, FL
$437 per night
Superhost
Home in Naples, Florida
Island lifestyle family vacation home (Salt Pool)
$192 per night
Superhost
Home in Cartagena, Colombia
Cartagena walled casa Mónaco
$631 per night
Superhost
Home in Fort Lauderdale, Florida
Beach area chic cabana home/pool/BBQ
$213 per night
Superhost
Home in Fort Lauderdale, Florida
Bamboo House/step 2 beach/Heated Pool/Spa
$523 per night
Superhost
Home in Rincon, Puerto Rico
Casa Ensenada- Rincon Puerto Rico
$381 per night
Superhost
Home in Fort Lauderdale, Florida
700 Home Private Pool: 2 Bed/1 Bath- Victoria Park
$296 per night
Superhost
Home in North Side, Cayman Islands
Ocean's Edge: Beachfront Home with Rooftop Views
$348 per night
Superhost
Home in Gros Islet, St. Lucia
Gorgeous 3BR2BA Oceanfront Villa w/Pool, Concierge
$875 per night
Superhost
Home in Lake Worth, Florida
Modern beach cottage with heated pool
$154 per night

Condo rentals in Caribbean

Superhost
Condo in Bavaro, Dominican Republic
Beachfront Condo -Sea View A-201 @Costa Atlantica
$176 per night
Superhost
Condo in Miami Beach, Florida
Fontainebleau Hotel Sorrento Ocean View Junior
$300 per night
Superhost
Condo in Carolina, Puerto Rico
Beach Front Condo with Endless Ocean Views
$336 per night
Superhost
Condo in Carolina, Puerto Rico
Front & BackyardBeach Studio For 2
$130 per night
Superhost
Condo in Miami, Florida
Waterfront Spacious Luxury 1 Bedroom IconBrickell
$210 per night
Superhost
Condo in Miami, Florida
Large Designer Condo, Unique Ocean Views, SmartTVs
$448 per night
Superhost
Condo in Carolina, Puerto Rico
Breathtaking Views, Direct Beach Access Remodeled!
$383 per night
Superhost
Condo in Kingston, Jamaica
Stunning smart apt with pool & amazing sunset view
$80 per night
Superhost
Condo in Miami Beach, Florida
Oceanfront 14th Floor Brand New Beachfront Flat
$129 per night
Superhost
Condo in Santo Domingo, Dominican Republic
AMAZING VIEWS CITY CENTER | 2BR +picuzzi+gym ✓
$64 per night
Superhost
Condo in Cartagena, Colombia
New apartment overlooking the private sea-Jacuzzi
$64 per night
Superhost
Condo in Montego Bay, Jamaica
Paradise Haven by the Sea.
$195 per night

Your guide to Caribbean

All About the Caribbean

The Caribbean is made up of 26 island countries surrounded by bejeweled blue and green waters and is known around the world as a holiday paradise. People flock here, especially in the winter, for warm sands, golden sunshine, and that sense of island time abandon — plus, the fruity drinks under towering palm trees. The Dominican Republic is the most visited of all the islands due to its vibrant city and cultural life and postcard-perfect beaches. West of that is Cuba, famous for its Old World architecture, rich jazz and music scenes, and several UNESCO World Heritage Sites. Closer to South America is little St. Lucia, known for its rainforests, colorful coral reefs (perfect for diving and snorkeling), and, of course, pristine beaches surrounded by the island’s volcanic peaks.

The countries in the Caribbean are extremely diverse, not only in their histories, cultures, and languages, but their landscapes and topographies. For example, vibrant Jamaica could not be more different from super-chill Aruba and swanky St. Barts. So whether you’re seeking an island that’s large or small, glitzy or low-key, in the Caribbean there is a sanctuary for everyone.


The best time to stay in a vacation rental in Caribbean

Thanks to trade winds, the weather in the Caribbean is sunny and pleasant all year round. The only caveat is that tropical storms and hurricanes occur to varying degrees of intensity here, and their likelihood increases from about July to November. But it’s the dry season from December through March that makes the region so popular. Villas to rent in the Caribbean are in demand during the winter, as many feel the urge to escape the colder weather up north and take in the sun, fun, and the many festivals — like Trinidad’s Carnival, the biggest of the Caribbean’s carnivals, and the Bahamas’ Junkanoo, a cultural street festival and celebration dating back centuries that takes place between Boxing and New Year’s Day. There are also plenty of Caribbean rentals in May and June, if you don’t mind the chance of a little rain.


Top things to do in Caribbean

Santo Domingo

Santo Domingo, the capital of the Dominican Republic, is the oldest continuously inhabited colonial settlement in the Western Hemisphere and was founded in 1496. The historic city center, Zona Colonial, is a UNESCO World Heritage Site, with cobblestone streets, colorful houses, and colonial-style architecture and structures like the 16th-century Basilica Cathedral of Santa María la Menor, the oldest surviving cathedral in the Americas.

Curaçao

Sitting off the coast of Venezuela is the Dutch island of Curaçao, lesser known than its neighbors, but with just as much to offer — including its lack of hurricane seasons. Willemstad, the capital, is one of the few UNESCO World Heritage cities in the Caribbean, and it’s pulsing with nightlife and festivals like Carnival and King’s Day. The diving here is top-notch, there are dozens of stunning beaches to choose from, and the lodging ranges from hostels to five-star resorts — so there’s something here for everyone.

Reggae in Jamaica

Jamaica is the birthplace of reggae. The music took off in the late 1960s, and by the 1970s, with the superstardom of Bob Marley and the Wailers, it became known throughout the world. If you’re in Kingston, check out the clubs, still playing the dub style that made the genre so popular. The best of the best musicians have been known to play at the annual reggae festival held in June.

Destinations to explore